Benzothiazole-tethered 1,2,3-triazoles: Synthesis, antimicrobial, antioxidant, and molecular docking studies

• Published in: Journal of molecular structure 2022-10, Vol.1266, p.133417, Article 133417
• Main Authors: Malah, Tamer El, Hegab, Mohamed I., Awad, Hassan M., Abdelrahman, Mohamad T., Abdel-Megeid, Farouk M.E., Shamroukh, Ahmed H., Mageid, Randa E. Abdel, Nour, Hany F.
• Format: Article
• Language: English
• Subjects: 1,2,3-triazole; Antimicrobial; Antioxidant; Benzothiazole; Molecular docking
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2022.133417

•The synthesis of novel benzothiazole-1,2,3-triazole derivatives 12–21 is described.•In vitro antimicrobial activity of derivatives 12–21 was investigated.•The antioxidant activity of the novel compounds 12–21 has been studied.•The compounds were more active aganist Gram-negative than Gram-positive bacteria.•All compounds significantly suppressed P. aeruginosa except for 17 and 18.•Compound 18 had a substantial antimicrobial effect against E. coli.•Compound 20 had significant efficacy against C. albicans.•Derivatives 17–19 exhibited remarkable antioxidant potential.•The most active compounds were able to form stable protein–ligand interactions. Over the past decades, antibiotic resistance has garnered considerable attention as a public health concern. Therefore, it has become necessary to develop new generations of antibacterial drugs. Here we describe the synthesis of novel benzothiazole-1,2,3-triazoles 12–21 utilizing copper(I) catalyzed alkyne-azide cycloaddition reactions. Compounds 12–21 were tested for their in vitro antibacterial activity on Gram-positive and Gram-negative bacteria. Derivative 18 displayed high antibacterial activity against Escherichia coli. All compounds exhibited remarkable inhibitory effects against Pseudomonas aeruginosa, except for derivatives 17 and 18. Antifungal evaluation of compounds 12–21 revealed high activity of derivative 20 against Candida albicans. Among all the tested compounds, derivatives 17, 18, and 19 showed high antioxidant activity. Molecular docking studies were undertaken to validate the antibacterial results. Graphical Abstract [Display omitted] .